WO2002087536A1 - Utilisation de preparations cationiques - Google Patents

Utilisation de preparations cationiques Download PDF

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Publication number
WO2002087536A1
WO2002087536A1 PCT/EP2002/004374 EP0204374W WO02087536A1 WO 2002087536 A1 WO2002087536 A1 WO 2002087536A1 EP 0204374 W EP0204374 W EP 0204374W WO 02087536 A1 WO02087536 A1 WO 02087536A1
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WIPO (PCT)
Prior art keywords
acid
carbon atoms
use according
alkyl
esterquats
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PCT/EP2002/004374
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German (de)
English (en)
Inventor
Esther Prat Queralt
Cristina Amela Conesa
Original Assignee
Cognis Iberia, S.L.
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Priority to JP2002584882A priority Critical patent/JP2004527550A/ja
Priority to US10/476,553 priority patent/US20040146478A1/en
Publication of WO2002087536A1 publication Critical patent/WO2002087536A1/fr

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    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K8/00—Cosmetics or similar toiletry preparations
    • A61K8/18—Cosmetics or similar toiletry preparations characterised by the composition
    • A61K8/30—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds
    • A61K8/40—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds containing nitrogen
    • A61K8/42—Amides
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K8/00—Cosmetics or similar toiletry preparations
    • A61K8/18—Cosmetics or similar toiletry preparations characterised by the composition
    • A61K8/30—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds
    • A61K8/40—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds containing nitrogen
    • A61K8/41—Amines
    • A61K8/416—Quaternary ammonium compounds
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K8/00—Cosmetics or similar toiletry preparations
    • A61K8/18—Cosmetics or similar toiletry preparations characterised by the composition
    • A61K8/30—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds
    • A61K8/40—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds containing nitrogen
    • A61K8/45—Derivatives containing from 2 to 10 oxyalkylene groups
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61Q—SPECIFIC USE OF COSMETICS OR SIMILAR TOILETRY PREPARATIONS
    • A61Q19/00—Preparations for care of the skin
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61Q—SPECIFIC USE OF COSMETICS OR SIMILAR TOILETRY PREPARATIONS
    • A61Q5/00—Preparations for care of the hair
    • A61Q5/12—Preparations containing hair conditioners
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61Q—SPECIFIC USE OF COSMETICS OR SIMILAR TOILETRY PREPARATIONS
    • A61Q5/00—Preparations for care of the hair
    • A61Q5/006—Antidandruff preparations

Definitions

  • the invention is in the field of cosmetics and relates to the use of mixtures of esterquats and fatty acid amidoamines for the production of cosmetic preparations, especially those for hair care.
  • Cationic surfactants generally have the property of being absorbed onto the negatively charged keratin fibers. They create a repulsive effect between the filaments, which means that the hair is easier to comb, less electrically charged and feels softer overall. Occasionally, the gloss is also improved. Although this is, as already mentioned, a more or less generic property of the cationic surfactants, the effects to be achieved are of course strongly dependent on the structure of the species used or their successful mixing. Since there is a practically unlimited number of cationically charged surface-active substances, there is no need to permute them among each other in order to open up a tremendous range of possibilities within which new preparations with interesting or even specially tailored properties can be found at any time ,
  • the object of the invention was to provide transparent cosmetic preparations, especially for hair care and in particular for hair conditioning, which allow both silicone oils and antidandruff active ingredients to be incorporated, which are stable in terms of storage and temperature.
  • soft touch and anti-static treatment of the hair should at least reach the level of the prior art.
  • the invention relates to the use of mixtures containing
  • esters (component a) is generally understood to mean quaternized fatty acid alkanolamine ester salts. These are known substances that can be obtained using the relevant methods of preparative organic chemistry.
  • German patent DE 4308794 Cl (Henkel) also describes a process for the preparation of solid ester quats is known in which the quaternization of triethanolamine esters is carried out in the presence of suitable dispersants, preferably fatty alcohols.
  • R ⁇ O represents an acyl radical having 6 to 22 carbon atoms
  • R 2 and R 3 independently of one another are hydrogen or R ⁇ O
  • R 4 represents an alkyl radical having 1 to 4 carbon atoms or a (CH 2 CH 2 O) q H- Group
  • m, n and p in total stands for 0 or numbers from 1 to 12
  • X for halide, alkyl sulfate or alkyl phosphate.
  • ester quats which can be used in the context of the invention are products based on caproic acid, caprylic acid, capric acid, lauric acid, myristic acid, palmitic acid, isostearic acid, stearic acid, oleic acid, elaidic acid, arachic acid, behenic acid and erucic acid and their technical mixtures , as they occur, for example, in the pressure splitting of natural fats and oils.
  • the fatty acids and the triethanolamine are used in a molar ratio of 1.1: 1 to 3: 1.
  • an application ratio of 1.2: 1 to 2.2: 1, preferably 1.5: 1 to 1.9: 1 has proven to be particularly advantageous.
  • the preferred esterquats are technical mixtures of mono-, di- and triesters with an average degree of esterification of 1.5 to 1.9 and are derived from C 8 -Cio-preliminary fatty acid, tallow fatty acid, palm fatty acid, coconut fatty acid, oleic acid, ricinoleic acid and their hardening products and mixtures (iodine number 0 to 40).
  • quaternized fatty acid triethanolamine ester salts of the formula (I) have proven to be particularly advantageous in which R ⁇ O for an acyl radical having 16 to 18 carbon atoms, R 2 for R ⁇ O, R 3 for hydrogen, R 4 for a methyl group, m , n and p is 0 and X is methyl sulfate.
  • R ⁇ O for an acyl radical having 16 to 18 carbon atoms
  • R 2 for R ⁇ O
  • R 3 for hydrogen
  • R 4 for a methyl group
  • m , n and p is 0
  • X is methyl sulfate.
  • Corresponding products are on the market under the Dehyquart® AU brand (Cognis Deutschland GmbH).
  • quaternized ester salts of fatty acids with diethanolalkylamines of the formula (II) are also suitable as esterquats.
  • R ⁇ O stands for an acyl radical with 6 to 22 carbon atoms
  • R 2 for hydrogen or R ⁇ O
  • R 4 and R 5 independently of one another for alkyl radicals with 1 to 4 carbon atoms
  • m and n in total for 0 or numbers from 1 to 12
  • X represents halide, alkyl sulfate or alkyl phosphate.
  • ester quats are the quaternized ester salts of fatty acids with 1,2-dihydroxypropyl dialkylamines of the formula (III)
  • R ⁇ O for an acyl radical having 6 to 22 carbon atoms
  • R 2 for hydrogen or R ⁇ O
  • R 4 , R 6 and R 7 independently of one another for alkyl radicals with 1 to 4 carbon atoms
  • m and n in total for 0 or numbers from 1 to 12
  • X represents halide, alkyl sulfate or alkyl phosphate.
  • ester quats are substances in which the ester bond is replaced by an amide bond and which preferably follow the formula (IV) based on diethylenetriamine,
  • amide ester quats are available on the market, for example, under the Incroquat® (Croda) brand.
  • esterquats are also substances which are obtainable on the basis of ethoxylated castor oil or its hardening products and preferably follow the formula (V)
  • R 8 CO for a saturated and / or unsaturated ethoxylated hydroxyacyl radical having 16 to 22, preferably 18 carbon atoms and 1 to 50 oxyethylene units
  • A for a linear or branched alkylene radical having 1 to 6 carbon atoms
  • R 9 , R 10 and R 11 independently from each other represent hydrogen or an alkyl group having 1 to 4 carbon atoms
  • R 12 represents an alkyl radical having 1 to 4 carbon atoms or a benzyl radical
  • X represents halogen, alkyl sulfate or alkyl phosphate.
  • Both fatty acids and the corresponding triglycerides can be used to prepare the esterquats of the formulas (I) to (V).
  • Such a method which is to be named as representative of the corresponding prior art, is proposed in the European patent EP 0750606 B1 (Cognis). It is also possible to carry out the condensation of the alkanolamines with the fatty acids in the presence of defined amounts of dicarboxylic acids, such as, for example, oxalic acid, malonic acid, succinic acid, maleic acid, fumaric acid, glutaric acid, adipic acid, sorbic acid, pimelic acid, azelaic acid, sebacic acid and / or dodecanedioic acid.
  • dicarboxylic acids such as, for example, oxalic acid, malonic acid, succinic acid, maleic acid, fumaric acid, glutaric acid, adipic acid, sorbic acid, pimelic acid, azelaic acid,
  • ester quats This results in a partially oligomeric structure of the ester quats, which can have an advantageous effect on the clear solubility of the products, particularly when adipic acid is also used.
  • Corresponding products under the brand Dehyquart® D 6003 (Cognis Deutschland GmbH) are commercially available and are described, for example, in European Patent EP 0770594 Bl (Cognis).
  • fatty acid amidoamines which form component (b) are known substances which can be obtained, for example, by reacting fatty acids with polyvalent ones in a manner known per se.
  • Substances of the formula (VI) are preferably used
  • R 13 represents a linear or branched, saturated or unsaturated acyl radical with 6 to 22 carbon atoms
  • R 14 and R 15 independently of one another for hydrogen, an optionally hydroxyl-substituted alkyl radical with 1 to 4 carbon atoms
  • B for a linear or branched alkylene group with 2 to 4 carbon atoms and n represents 1 or 2.
  • amide component is derived from ethylenediamine, propylenediamine, diethylenetriamine, dipropylenetriamine, aminoethylethanolamine and in particular N, N, -dimethylaminopropylamine and mixtures thereof.
  • the fatty acid amidoamines which combine the individual structural features mentioned as preferred are preferred.
  • esterquats and the fatty acid amidoamines in a weight ratio of 99.1: 0.1 to 10:90.
  • a ratio of 75: 25 to 25: 75 and in particular 60: 40 to 40: 60 has proven to be particularly advantageous, since synergistic performance gains are observed here.
  • the esterquats and the fatty acid amidoamines are used together with fatty alcohols and / or fatty alcohol polyglyco- lethern used.
  • fatty alcohols or fatty alcohol polyglycol ethers preferably follow the formula (VII),
  • R 16 represents a linear or branched alkyl and / or alkenyl radical having 6 to 22, preferably 12 to 18 carbon atoms and m represents 0 or numbers from 1 to 20, preferably 10 to 15.
  • Typical examples are caproic, caprylic, Capri-nalkohol, lauryl alcohol, myristyl alcohol, cetyl alcohol, stearyl, isostearyl, Oleylolakohol, elaidyl, petroselinyl, arachyl, gadoleyl, nylalkohol behenyl and erucyl alcohol and technical mixtures thereof such as co kosalkohol or Ceterylalkohol and their ethylene oxide adducts.
  • esterquats and fatty acid amidoamines on the one hand and the fatty alcohols or fatty alcohol polyglycol ethers on the other hand can again be used in a weight ratio of 90:10 to 10:90, a ratio of 35:65 to 50:50 being preferred here.
  • silicone oils and antidandruff agents which are usually difficult to incorporate into emulsions and which show the tendency to separate again after prolonged storage, especially when exposed to temperature.
  • Suitable silicone oils are, for example, dimethylpolysiloxanes, methylphenylpolysiloxanes, cyclic silicones as well as amino, fatty acid, alcohol, polyether, epoxy, fluorine, glycoside and / or alkyl modified silicone compounds, which can be both liquid and resinous at room temperature. Simethicones, which are mixtures of dimethicones with an average chain length of 200 to 300 dimethylsiloxane units and hydrogenated silicates, are also suitable. A detailed overview of suitable volatile silicones can also be found by Todd et al. in Cosm.Toil. 91, 27 (1976).
  • the silicone oils can be used in amounts of 1 to 20, preferably 5 to 15% by weight, based on the preparations.
  • Piroctone olamine (l-hydroxy-4-methyl-6- (2,4,4-tri-mythylpentyl) -2- (lH) -pyridinone monoethanolamine salt), Baypival® (Climbazole), Ketoconazol®, (4 -Acetyl-l - ⁇ - 4- [2- (2.4-dichlorophenyl) r-2- (lH-imidazol-l-ylmethyl) -l, 3-dioxylan-c- c-4-ylmethoxyphenyl ⁇ piperazine, ketoconazole, elubiol, selenium disulfide, sulfur colloidal, sulfur polyethyleneglycol sorbitan monooleate, sulfuric rinoleol polyhexoxate, sulfur tar distillates, salicylic acid (or in combination with hexachlorophene) undecylenate-unduccinate acid- undethylenediamine acid-undoxylenesulfonate acid-undex
  • Another object of the invention relates to the use of the mixtures of components (a) and (b) for the production of hair care products, especially hair conditioners, preferably those in emulsion form, which are in particular hair creams, each of which the mixtures in amounts from 1 to 30, preferably 2 to 20 and in particular 5 to 15 wt .-% - based on the preparations - can contain.
  • a final object of the invention relates to the use of the mixtures of components (a) and (b) for the production of skin care products, in particular those in emulsion form.
  • These cosmetic preparations can furthermore contain, as further auxiliaries and additives, mild surfactants, oil bodies, emulators, pearlescent waxes, consistency agents, thickeners, superfatting agents, stabilizers, polymers, fats, waxes, lecithins, phospholipids, biogenic active substances, UV light protection factors, antioxidants, deodorants, antiperspirants, film formers, swelling agents, insect repellents, self-tanners, tyrosine inhibitors (depigmentation agents), hydrotropes, solubilizers, preservatives, perfume oils, dyes and the like.
  • mild surfactants oil bodies, emulators, pearlescent waxes, consistency agents, thickeners, superfatting agents, stabilizers, polymers, fats, waxes, lecithins, phospholipids, biogenic active substances, UV light protection factors, antioxidants, deodorants, antiperspirants, film formers, swelling agents, insect repellents, self-tanners, tyrosine inhibitor
  • Anionic, nonionic and / or amphoteric or zwitterionic surfactants may be present as surface-active substances, the proportion of these agents usually being about 1 to 70, preferably 5 to 50 and in particular 10 to 30% by weight.
  • anionic surfactants are soaps, alkyl benzene sulfonates, alkane sulfonates, olefin sulfonates, alkyl ether sulfonates, glycerol ether sulfonates, ⁇ -methyl ester sulfonates, sulfate fatty acids, alkyl sulfates, fatty alcohol ether sulfates, glycerol ether sulfates, fatty acid ether sulfates, hydroxymate sulfate ethersulfate, hydroxymate sulfate ethersulfate, hydroxymate sulfate ethersulfate, hydroxymate sulfate ethers
  • anionic surfactants contain polyglycol ether chains, they can have a conventional, but preferably a narrow, homolog distribution.
  • Typical examples of nonionic surfactants are fatty alcohol polyglycol ethers, Al kylphenolpolyglycolether, fatty acid, FettTexreamidpolyglycol ether, fatty N-alkyl glucamides aminpolyglycolether, alkoxylated triglycerides, mixed ethers and mixed formals, optionally partially oxidized alk (en) yl oligoglycosides or glucuronic acid derivatives, fatty acid, protein hydrolysates (especially vegetable products based on wheat), polyol fatty acid esters, sugar esters, sorbita nests, polysorbates and amine oxides.
  • nonionic surfactants contain polyglycol ether chains, they can have a conventional, but preferably a narrow, homolog distribution.
  • Typical examples of amphoteric or zwitterionic surfactants are alkyl betaines, alkyl amido betaines, aminopropionates, aminoglycinates, imidazolinium betaines and sulfobetaines.
  • the surfactants mentioned are exclusively known compounds. With regard to the structure and manufacture of these substances, reference is made to relevant reviews, for example, J.Falbe (ed.), "Surfactants in Consumer Products", Springer Verlag, Berlin, 1987, pp.
  • particularly skin-compatible surfactants are fatty alcohol polyglycol ether, midobetaine monoglyceride sulfates, mono- and / or dialkyl sulfosuccinates, fatty acid taurides, fatty acid glutamates, ⁇ -olefin sulfonates, ethercarboxylic acids, alkyl oligoglucosides, fatty acid glucamides, alkylamine, amphoacetals and / or protein fatty acid condensates, the latter preferably based on wheat proteins.
  • Guerbet alcohols based on fatty alcohols having 6 to 18, preferably 8 to 10 carbon atoms, esters of linear C 6 -C 22 fatty acids come as oil bodies with linear or branched C 6 -C 22 fatty alcohols or esters of branched C 6 -C 13 carboxylic acids with linear or branched C 6 -C 22 fatty alcohols, such as myristyl myristate, myristyl palmitate, myristyl stearate, myristyle isostea rat, myristyl, Myristylbehenat, Myristylerucat, cetyl myristate, Cetylpal itat, sostearat cetyl stearate, Cetylisostearat, cetyl oleate, cetyl behenate, Cetylerucat, Stearylmyristat, Stearylpa Copy, stearyl stearate, Stearyli-, stearyl oleate
  • esters of linear C 6 -C 22 fatty acids with branched alcohols in particular 2-ethylhexanol
  • esters of C 8 -C 38 alkyl hydroxycarboxylic acids with linear or branched C5-C 22 fatty alcohols cf.
  • dioctyl malates esters of linear and / or branched fatty acids with polyhydric alcohols (such as propylene glycol, dimer diol or trimer triol) and / or Guerbet alcohols, triglycerides based on Cs-C ⁇ 0 fatty acids, liquid mono7di / triglyceride mixtures based on C 6 -C ⁇ 8 fatty acids, esters of C 6 -C 22 fatty alcohols and / or Guerbet alcohols with aromatic carboxylic acids, especially benzoic acid, esters of C 2 -C 2 -dicarboxylic acids with linear or branched alcohols with 1 to 22 carbon atoms or polyols with 2 to 10 carbon atoms and 2 to 6 hydroxyl groups, vegetable oils, branched primary alcohols, substituted cyclohexanes, linear and branched C 6 -C 22 fatty alcohol carbonates, such as Dicaprylyl carbon
  • Finsolv® TN linear or branched, symmetrical or asymmetrical dialkyl ethers with 6 to 22 carbon atoms per alkyl group, such as dicaprylyl ether (Cetiol® OE), ring opening products of epoxidized fatty acid esters with polyols and / or aliphatic or naphthenic hydrocarbons, such as squalane, squalene or dialkylcyclohexanes.
  • dicaprylyl ether such as dicaprylyl ether (Cetiol® OE)
  • ring opening products of epoxidized fatty acid esters with polyols and / or aliphatic or naphthenic hydrocarbons such as squalane, squalene or dialkylcyclohexanes.
  • Suitable emulsifiers are nonionic surfactants from at least one of the following groups:
  • Partial esters of polyglycerol (average degree of self-condensation 2 to 8), polyethylene glycol (molecular weight 400 to 5000), trimethylolpropane, pentaerythritol, sugar alcohols (e.g. sorbitol), alkyl glucosides (e.g. methyl glucoside, butyl glucoside, lauryl glucoside) and polyglucosides saturated (e.g. cellulose / or unsaturated, linear or branched fatty acids with 12 to 22 carbon atoms and / or hydroxycarboxylic acids with 3 to 18 carbon atoms and their adducts with 1 to 30 moles of ethylene oxide;
  • Polymer emulsifiers e.g. Pemulen types (TR-1, TR-2) from Goodrich;
  • the adducts of ethylene oxide and / or of propylene oxide with fatty alcohols, fatty acids, alkylphenols or with castor oil are known, commercially available products. These are mixtures of homologues, the average degree of alkoxylation of which is the ratio of the amounts of ethylene oxide and / or pro- pylene oxide and substrate with which the addition reaction is carried out corresponds.
  • C ⁇ 2 / ⁇ 8 fatty acid monoesters and diesters of adducts of ethylene oxide with glycerol are known from DE 2024051 PS as refatting agents for cosmetic preparations.
  • Alkyl and / or alkenyl oligoglycosides their preparation and their use are known from the prior art. They are produced in particular by reacting glucose or oligosaccharides with primary alcohols with 8 to 18 carbon atoms.
  • the glycoside residue both monoglycosides in which a cyclic sugar residue is glycosidically bonded to the fatty alcohol and oligomeric glycosides with a degree of oligomerization of up to about 8 are suitable.
  • the degree of oligomerization is a statistical mean value which is based on a homolog distribution customary for such technical products.
  • Suitable partial glycerides are Hydroxystearin Textremonogly- cerid, hydroxystearic acid diglyceride, isostearic acid, Isostearinklare- diglyceride, oleic acid monoglyceride, oleic acid diglyceride klarediglycerid, Ricinolklaremoglycerid, ricinoleic, Linolklaremonoglycerid, Linolklarediglycerid, LinolenTalkremonogly- cerid, LinolenLiterediglycerid, Erucaklaklamonoglycerid, Erucaklaklarediglycerid, tartaric acid monoglyceride, Weinchurediglycerid, Citronenklamonoglycerid, Citric diglyceride, malic acid monoglyceride, malic acid diglyceride and their technical mixtures, which may still contain small amounts of triglyceride from the manufacturing process. Addition products of 1 to 30,
  • polyglycerol esters are polyglyceryl-2 dipolyhydroxystearate (Dehymuls® PGPH), polyglycerol-3-diisostearate (Lameform® TGI), polyglyceryl-4 isostearate (Isolan® GI 34), polyglyceryl-3 oleate, diisostearoyl po- lyglyceryl-3 diisostearate (Isolan® PDI), polyglyceryl-3 methylglucose distearate (Tego Care® 450), polyglyceryl-3 beeswax (Cera Bellina®), polyglyceryl-4 caprate (polyglycerol caprate T2010 / 90), polyglyceryl-3 cetyl ether ( Chimexane® NL), Polyglyceryl-3 Distearate (Cremophor® GS 32) and Polyglyceryl Polyricinoleate (Admul® WOL 1403) Polyglyceryl Dimer
  • polystyrene resin examples include the mono-, di- and triesters of trimethylolpropane or pentaerythritol, if appropriate reacted with 1 to 30 mol of ethylene oxide, with lauric acid, coconut fatty acid, tallow fatty acid, palmitic acid, stearic acid, oleic acid, behenic acid and the like.
  • Typical anionic emulsifiers are aliphatic fatty acids with 12 to 22 carbon atoms, such as, for example, palmitic acid, stearic acid or behenic acid, and dicarboxylic acids with 12 to 22 carbon atoms, such as, for example, azelaic acid or sebacic acid.
  • Zwitterionic surfactants can also be used as emulsifiers.
  • Zwitterionic surfactants are surface-active compounds that contain at least one quaternary ammonium group and at least one in the molecule Wear carboxylate and a sulfonate group.
  • Particularly suitable zwitterionic surfactants are the so-called betaines such as the N-alkyl-N, N-dimethylammonium glycinate, for example coconut alkyldimethylammonium glycinate, N-acylaminopropyl-N, N-dimethylammonium glycinate, for example coconut acylaminopropyldimethylammonium glycinate, and 2-alkyl -3-carboxylmethyl-3-hydroxyethylimidazolines each having 8 to 18 carbon atoms in the alkyl or acyl group, and also the cocosacylaminoethylhydroxyethylcarboxymethylglycinate.
  • betaines such as the N-alkyl-N, N-dimethylammonium glycinate, for example coconut alkyldimethylammonium glycinate, N-acylaminopropyl-N, N-dimethylammonium glyc
  • Suitable emulsifiers are ampholytic surfactants.
  • Those surface-active compounds are Ampholytic Ten ⁇ iden which, apart from a C 8 ⁇ 8 alkyl or acyl group, contain at least one free amino group and at least one -COOH or -SO 3 H group and contain internal to form salts are capable ,
  • suitable ampholytic surfactants are N-alkylglycine, N-alkylpropionic acid, N-alkylaminobutyric acid, N-alkyliminodipropionic acid, N-hydroxyethyl-N-alkylamidopropylglycine, N-alkyltaurine, N-alkyl sarcosine, 2-alkylaminopropionic acid and alkylaminoacetic acid with in each case about 8 to 18 carbon atoms in the alkyl group ..
  • ampholytic surfactants are N-Kokosal- kylaminopropionat, cocoacylaminoethyl aminopropionate and C ⁇ 2 / ⁇ cosin 8 -Acylsar-.
  • cationic surfactants are also suitable as emulsifiers, those of the esterquat type, preferably methyl-quaternized difatty acid triethanolamine ester salts, being particularly preferred.
  • Typical examples of fats are glycerides, ie solid or liquid vegetable or animal products which essentially consist of mixed glycerol esters of higher fatty acids
  • waxes include natural waxes such as candelilla wax, carnauba wax, Japanese wax, esparto grass wax, cork wax, guaruma wax, rice germ oil - wax, sugar cane wax, ouricury wax, montan wax, beeswax, shellac wax, walrus, lanolin (wool wax), pretzel fat, ceresin, ozokerite (earth wax), petrolatum, paraffin waxes, micro waxes; chemically modified waxes (hard waxes), such as montan ester waxes, Sasol waxes, hydrogenated jojoba waxes and synthetic waxes, such as polyalkylene waxes and polyethylene glycol waxes.
  • natural waxes such as candelilla wax, carnauba wax, Japanese wax, esparto
  • fat-like substances such as leine lead and phospholipids can also be used as additives.
  • the term Leeithine is understood by those skilled in the art to mean those glycerophospholipids which form from fatty acids, glycerol, phosphoric acid and choline by esterification. Leeithine are therefore often referred to in the professional world as phosphatidyl choline (PC). Examples of natural Leeithine include the cephalins, which are also referred to as phosphatidic acids and represent derivatives of 1,2-diacyl-sn-glycerol-3-phosphoric acids.
  • phospholipids are usually understood to be mono- and preferably diesters of phosphoric acid with glycerol (glycerol phosphates), which are generally classed as fats.
  • glycerol phosphates glycerol phosphates
  • sphingosines or sphingolipids are also suitable.
  • Pearlescent waxes that can be used are, for example: alkylene glycol esters, especially ethylene glycol distearate; Fatty acid alkanolamides, especially coconut fatty acid diethanolamide; Partial glycerides, especially stearic acid monoglyceride; Esters of polyvalent, optionally hydroxy-substituted carboxylic acids with fatty alcohols having 6 to 22 carbon atoms, especially long-chain esters of tartaric acid; Fatty substances, such as, for example, fatty alcohols, fatty ketones, fatty aldehydes, fatty ethers and fatty carbonates, which have a total of at least 24 carbon atoms, especially lauron and distearyl ether; Fatty acids such as stearic acid, hydroxystearic acid or behenic acid, ring opening products of olefin epoxides with 12 to 22 carbon atoms with fatty alcohols with 12 to 22 carbon atoms and / or polyols with 2 to 15
  • Suitable consistency agents are primarily fatty alcohols or hydroxy fatty alcohols with 12 to 22 and preferably 16 to 18 carbon atoms and, in addition, partial glycerides, fatty acids or hydroxy fatty acids.
  • a combination of these substances with alkyl oligoglucosides and / or fatty acid N-methylglucamides of the same chain length and / or polyglycerol poly-12-hydroxystearates is preferred.
  • Suitable thickeners are, for example, Aerosil types (hydrophilic silicas), polysaccharides, in particular xanthan gum, guar guar, agar agar, alginates and tyloses, carboxymethyl cellulose and hydroxyethyl and hydroxypropyl cellulose, and also higher molecular weight polyethylene glycol mono- and diesters of fatty acids, Polyacrylates, (e.g. Carbopole® and Pemulen types from Goodrich; Synthalene® from Sigma; Keltrol types from Kelco; Sepigel types from Seppic; Salcare types from Allied Colloids), polyacrylamides, polymers, polyvinyl alcohol and polyvinyl pyrrolidone.
  • Aerosil types hydrophilic silicas
  • polysaccharides in particular xanthan gum, guar guar, agar agar, alginates and tyloses, carboxymethyl cellulose and hydroxyethyl and hydroxypropyl
  • Bentonites such as Bentone® Gel VS-5PC (Rheox), which is a mixture of cyclo- pentasiloxane, disteardimonium hectorite and propylene carbonate.
  • Surfactants such as, for example, ethoxylated fatty acid glycerides, esters of fatty acids with polyols such as, for example, pentaerythritol or trimethylolpropane, fatty alcohol ethoxylates with a narrow homolog distribution or alkyl oligoglucosides and electrolytes such as sodium chloride and ammonium chloride are also suitable.
  • Substances such as, for example, lanolin and lecithin and polyethoxylated or acylated lanolin and lecithin derivatives, polyol fatty acid esters, monoglycerides and fatty acid alkanolamides can be used as superfatting agents, the latter simultaneously serving as foam stabilizers.
  • Metal salts of fatty acids such as e.g. Magnesium, aluminum and / or zinc stearate or ricinoleate are used.
  • Suitable cationic polymers are, for example, cationic cellulose derivatives, such as, for example, a quaternized hydroxyethyl cellulose, which is available from Amerchol under the name Polymer JR 400®, cationic starch, copolymers of diallylammonium salts and acrylamides, quaternized vinylpyrrolidone / vinylimidazole polymers, such as, for example, Luviquat® ( BASF), condensation products of polyglycols and amines, quaternized collagen polypeptides, such as, for example, lauryldimonium hydroxypropyl hydrolyzed collagen (Lamequat®L / Grünau), quaternized wheat polypeptides, polyethyleneimine, cationic silicone polymers, such as amodimethicones, copolymers of adipic acid and di-methylozarino-hydroxypropyl (dimethylamino-hydroxypropyl) ), Copolymers of acrylic
  • Anionic, zwitterionic, amphoteric and nonionic polymers include, for example, vinyl acetate / crotonic acid copolymers, vinylpyrrolidone / vinyl acrylate copolymers, vinyl acetate / butyl maleate / isobornyl acrylate copolymers, methyl vinyl ether / maleic anhydride copolymers and polyesters and their esters, non-polyesters and their acrylates , Acrylamidopropyltrimethylammonium chloride / acrylate copolymers, octyl acrylamide / methyl methacrylate / tert.butylaminoethyl methacrylate / 2-hydroxypropyl meth acrylate copolymers, polyvinylpyrrolidone, vinylpyrrolidone / vinyl acetate copolymers, vinylpyrrolidone / dimethylaminoethylroloyl methacrylate and optionally
  • UV light protection factors are understood to mean, for example, organic substances (light protection filters) which are liquid or crystalline at room temperature and which are able to absorb ultraviolet rays and absorb the energy absorbed in the form of longer-wave radiation, e.g. To give off heat again.
  • UVB filters can be oil-soluble or water-soluble. As oil-soluble substances e.g. to call:
  • 4-aminobenzoic acid derivatives preferably 2-ethylhexyl 4- (dimethylamino) benzoate, 2-octyl 4- (dimethylamino) benzoate and amyl 4- (dimethylamino) benzoate;
  • esters of cinnamic acid preferably 4-methoxycinnamic acid 2-ethylhexyl ester, 4-methoxycinnamic acid propyl ester, 4-methoxycinnamic acid isoamyl ester 2-cyano-3,3-phenylcinnamic acid 2-ethylhexyl ester (octocrylene);
  • esters of salicylic acid preferably salicylic acid 2-ethylhexyl ester, salicylic acid 4-iso-propylbenzyl ester, salicylic acid homomethyl ester;
  • benzophenone preferably 2-hydroxy-4-methoxybenzophenone, 2-hydroxy-4-methoxy-4 , -methylbenzophenone, 2,2 x -dihydroxy-4-methoxybenzophenone;
  • Esters of benzalmalonic acid preferably di-2-ethylhexyl 4-methoxybenzmalonate; > Triazine derivatives, such as 2,4,6-trianilino- (p-carbo-2 , -ethyl-r-hexyloxy) -l, 3,5-triazine and octyl triazone, as described in EP 0818450 AI or dioctyl butamido triazone (Uvasorb® HEB);
  • Propane-1,3-diones such as 1- (4-tert-butylphenyl) -3- (4 ⁇ methoxyphenyl) propane-1,3-dione;
  • Typical UV-A filters are, in particular, derivatives of benzoyl methane such as l- (4, -tert.Butylphenyl) -3- (4-methoxyphenyl) propan-l, 3-dione, 4-tert-butyl -4 ⁇ - methoxydibenzoylmethane (Parsol® 1789), l-phenyl-3- (4 ⁇ -isopropylphenyl) -propane-l, 3-dione and enamine compounds as described in DE 19712033 AI (BASF).
  • the UV-A and UV-B filters can of course also be used in mixtures.
  • Particularly favorable combinations consist of the derivatives of benzoylmethane, for example 4-tert-butyl-4 , methoxydibenzoylmethane (Parsol® 1789) and 2-cyano-3,3-phenylcinnamic acid-2-ethylhexyl ester (octocrylene) in Combination with ester of cinnamic acid, preferably 2-ethylhexyl 4-methoxycinnamate and / or propyl 4-methoxycinnamate and / or isoamyl 4-methoxycinnamate.
  • benzoylmethane for example 4-tert-butyl-4 , methoxydibenzoylmethane (Parsol® 1789) and 2-cyano-3,3-phenylcinnamic acid-2-ethylhexyl ester (octocrylene) in Combination with ester of cinnamic acid, preferably 2-ethylhex
  • water-soluble filters such as, for example, 2-phenylbenzimidazole-5-sulfonic acid and its alkali metal, alkaline earth metal, ammonium, alkylammonium, alkanolammonium and glucammonium salts.
  • insoluble light protection pigments namely finely dispersed metal oxides or salts
  • suitable metal oxides are, in particular, zinc oxide and titanium dioxide and, in addition, oxides of iron, zirconium, silicon, manganese, aluminum and cerium and mixtures thereof.
  • Silicates (talc), barium sulfate or zinc stearate can be used as salts.
  • the oxides and salts are used in the form of the pigments for skin-care and skin-protecting emulsions and decorative cosmetics.
  • the particles should be medium Have diameters of less than 100 nm, preferably between 5 and 50 nm and in particular between 15 and 30 nm.
  • the pigments can also be surface-treated, ie hydrophilized or hydrophobicized.
  • Typical examples are coated titanium dioxides, such as titanium dioxide T 805 (Degussa) or Eusolex® T2000 (Merck). Silicones, and in particular trialkoxyoctylsilanes or simethicones, are particularly suitable as hydrophobic coating agents. So-called micro- or nanopigments are preferably used in sunscreens. Micronized zinc oxide is preferably used.
  • Other suitable UV light protection filters are the overview by P.Finkel in S ⁇ FW-Journal 122, 543 (1996) and Parf.Kosm. 3_, 11 (1999).
  • secondary light stabilizers of the antioxidant type can also be used, which interrupt the photochemical reaction chain which is triggered when UV radiation penetrates the skin.
  • Typical examples are amino acids (e.g. glycine, histidine, tyrosine, tryptophan) and their derivatives, imidazoles (e.g. urocanic acid) and their derivatives, peptides such as D, L-carnosine, D-carnosine, L-carnosine and their derivatives (e.g. anse- rin), carotenoids, carotenes (e.g.
  • ⁇ -carotene, ⁇ -carotene, lycopene and their derivatives, chlorogenic acid and their derivatives, lipoic acid and their derivatives (e.g. dihydroliponic acid), aurothioglucose, propylthiouracil and other thiols (e.g.
  • (metal) chelators e.g. ⁇ -hydroxy fatty acids, palmitic acid, phytic acid, lactoferrin), ⁇ -hydroxy acids (e.g. citric acid, lactic acid, malic acid), humic acid, bile acid, bile extracts, bilirubin , Biliverdin, EDTA, EGTA and their derivatives, unsaturated fatty acids and their derivatives (e.g. ⁇ -linolenic acid, linoleic acid, oleic acid), folic acid and their derivatives, ubiquinone and ubiquinol and their derivatives, vitamin C and derivatives (e.g.
  • biogenic active ingredients include tocopherol, tocopherol acetate, tocopherol palmitate, ascorbic acid, (deoxy) ribonucleic acid and its fragmentation products, ⁇ -glucans, retinol, bisabolol, allantoin, phytantriol, panthenol, AHA acids, amino acids, ceramides, essentil oils, pseudoceramides Plant extracts, such as To understand prunus extract, Bambaranus extract and vitamin complexes.
  • Cosmetic deodorants counteract, mask or eliminate body odors.
  • Body odors arise from the action of skin bacteria on apocrine sweat, whereby unpleasant smelling breakdown products are formed. Accordingly, deodorants contain active ingredients which act as germ-inhibiting agents, enzyme inhibitors, odor absorbers or odor maskers.
  • germ-inhibiting agents such as.
  • Esterase inhibitors are suitable as enzyme inhibitors. These are preferably trialkyl citrates, such as trimethyl citrate, tripropyl citrate, tri-isopropyl citrate, tributary guide and in particular triethyl guide (Hydagen® CAT). The substances inhibit enzyme activity and thereby reduce odor.
  • trialkyl citrates such as trimethyl citrate, tripropyl citrate, tri-isopropyl citrate, tributary guide and in particular triethyl guide (Hydagen® CAT).
  • the substances inhibit enzyme activity and thereby reduce odor.
  • esterase inhibitors include sterolsulfates or phosphates, such as, for example, lanosterol, cholesterol, campesterin, stigmasterol and sitosterol sulfate or phosphate, dicarboxylic acids and their esters, such as, for example, glutaric acid, monoethyl glutarate, Diethyl glutarate, adipic acid, monoethyl adipate, diethyl adipate, malonic acid and diethyl malonate, hydroxycarboxylic acids and their esters such as, for example, citric acid, malic acid, tartaric acid or tartaric acid diethyl ester, and zinc glycineate.
  • sterolsulfates or phosphates such as, for example, lanosterol, cholesterol, campesterin, stigmasterol and sitosterol sulfate or phosphate
  • dicarboxylic acids and their esters such as, for example, glutaric acid, monoeth
  • Suitable odor absorbers are substances that absorb odor-forming compounds and can retain them to a large extent. They lower the partial pressure of the individual components and thus also reduce their speed of propagation. It is important that perfumes must remain unaffected. Odor absorbers are not effective against bacteria. They contain, for example, a complex zinc salt of ricinoleic acid or special, largely odorless fragrances, which are known to the person skilled in the art as "fixators", such as, for example, the main component. B. extracts of Labdanum or Styrax or certain abietic acid derivatives. Fragrance agents or perfume oils act as odor maskers and, in addition to their function as odor maskers, give the deodorants their respective fragrance.
  • Perfume oils are, for example, mixtures of natural and synthetic fragrances. Natural fragrances are extracts of flowers, stems and leaves, fruits, fruit peels, roots, woods, herbs and grasses, needles and branches as well as resins and balms. Animal raw materials, such as civet and castoreum, are also suitable. Typical synthetic fragrance compounds are products of the ester, ether, aldehyde, ketone, alcohol and hydrocarbon type.
  • Fragrance compounds of the ester type are, for example, benzyl acetate, p-tert-butylcyclohexyl acetate, linalyl acetate, phenylethyl acetate, linalyl benzoate, benzyl formate, allyl cyclohexyl propionate, styrallyl propionate and benzyl salicylate.
  • the ethers include, for example, benzyl ethyl ether, the aldehydes, for example, the linear ones Alkanals with 8 to 18 carbon atoms, citral, citronellal, citronellyloxyacetalde- hyd, cyclamenaldehyde, hydroxycitronellal, lilial and bourgeonal, for the ketones, for example the jonones and methylcedryl ketone, for the alcohols anethole, citronellol, eugenol, isoeugenol, phenanylethyl alcohol, linalool and terpineol, the hydrocarbons mainly include the terpenes and balms.
  • fragrance oils of lower volatility which are mostly used as aroma components, are also suitable as perfume oils, e.g. sage oil, chamomile oil, clove oil, lemon balm oil, mint oil, cinnamon leaf oil, linden blossom oil, juniper berry oil, vetiver oil, oliban oil, galbanum oil, labdanum oil and lavandin oil.
  • Antiperspirants reduce sweat formation by influencing the activity of the eccrine sweat glands and thus counteract armpit wetness and body odor.
  • Aqueous or anhydrous formulations of antiperspirants typically contain the following ingredients:
  • non-aqueous solvents such as As ethanol, propylene glycol and / or glycerin.
  • Salts of aluminum, zirconium or zinc are particularly suitable as astringent antiperspirant active ingredients.
  • suitable antihydrotically active ingredients are, for example, aluminum chloride, aluminum chlorohydrate, aluminum sealant. lorhydrate, aluminum sesquichlorohydrate and their complex compounds z.
  • conventional oil-soluble and water-soluble auxiliaries can be present in smaller amounts in antiperspirants. Examples of such oil-soluble auxiliaries are:
  • water-soluble additives are e.g. Preservatives, water-soluble fragrances, pH adjusters, e.g. Buffer mixtures, water soluble thickeners, e.g. water-soluble natural or synthetic polymers such as e.g. Xanthan gum, hydroxyethyl cellulose, polyvinyl pyrrolidone or high molecular weight polyethylene oxides.
  • Common film formers are, for example, chitosan, microcrystalline chitosan, quaternized chitosan, polyvinylpyrrolidone, vinylpyrrolidone-vinyl acetate copolymers, polymers of the acrylic acid series, quaternary cellulose derivatives, collagen, hyaluronic acid or its salts and similar compounds.
  • Montmorillonites, clay minerals, pemulene and alkyl-modified carbopol types can serve as swelling agents for aqueous phases. Further suitable polymers or swelling agents can be found in the overview by R. Lochhead in Cosm.Toil. 108, 95 (1993).
  • Possible insect repellents are N, N-diethyl-m-toluamide, 1,2-pentanediol or ethyl butylacetylaminopropionate Self-tanners and depiqmentants
  • Dihydroxyacetone is suitable as a self-tanner.
  • Arbutin, ferulic acid, kojic acid, coumaric acid and ascorbic acid (vitamin C) can be used as tyrosine inhibitors, which prevent the formation of melanin and are used in depigmenting agents.
  • Hydrotropes such as, for example, ethanol, isopropyl alcohol or polyols, can also be used to improve the flow behavior.
  • Polyols that come into consideration here preferably have 2 to 15 carbon atoms and at least two hydroxyl groups.
  • the polyols can also contain further functional groups, in particular amino groups, or be modified with nitrogen. Typical examples are
  • Alkylene glycols such as, for example, ethylene glycol, diethylene glycol, propylene glycol, butylene glycol, hexylene glycol and polyethylene glycols with an average molecular weight of 100 to 1,000 daltons;
  • Methyl compounds such as in particular trimethylolethane, trimethylolpropane, trimethylolbutane, pentaerythritol and dipentaerythritol;
  • Dialcohol amines such as diethanolamine or 2-amino-l, 3-propanediol.
  • Suitable preservatives are, for example, phenoxyethanol, formaldehyde solution, parabens, pentanediol or sorbic acid and those known under the name Surfa- a known silver complex and the other substance classes listed in Appendix 6, Parts A and B of the Cosmetics Ordinance.
  • Perfume oils include mixtures of natural and synthetic fragrances. Natural fragrances are extracts of flowers (lily, lavender, roses, jasmine, neroli, ylang-ylang), stems and leaves (geranium, patchouli, petitgrain), fruits (anise, coriander, caraway, juniper), fruit peel (bergamot, lemon, Oranges), roots (mace, angelica, celery, cardamom, costus, iris, calmus), wood (pine, sandal, guaiac, cedar, rosewood), herbs and grasses (tarragon, lemongrass, sage, thyme), Needles and twigs (spruce, fir, pine, mountain pine), resins and balms (galbanum, elemi, benzoin, myrrh, olibanum, opoponax).
  • Typical synthetic fragrance compounds are products of the ester, ether, aldehyde, ketone, alcohol and hydrocarbon type. Fragrance compounds of the ester type are, for example, benzyl acetate, phenoxyethyl isobutyrate, p-tert-butylcyclohexyl acetate, linalyl acetate, dimethylbenzylcarbinylacetate, phenylethyl acetate, linalyl benzoate, benzyl formate, ethyl methylphenyl glycinate, allylcyclohexyl benzylatepylpropylate, stylate propionate, stylate propionate.
  • the ethers include, for example, benzylethyl ether
  • the aldehydes include, for example, the linear alkanals having 8 to 18 carbon atoms, citral, citronellal, citronellyloxyacetaldehyde, cyclamenaldehyde, hydroxycitronellal, lilial and bourgeonal
  • the ketones include, for example, the joonons, ⁇ -isomethylionone and methylcedryl ketone the alcohols anethole, citronellol, eugenol, isoeugenol, geraniol, linalool, phenylethyl alcohol and terpineol
  • the hydrocarbons mainly include the terpenes and balsams.
  • fragrance oils of lower volatility which are mostly used as aroma components, are also suitable as perfume oils, for example sage oil, chamomile oil, clove oil, lemon balm oil, mint oil, cinnamon leaf oil, linden blossom oil, juniper berry oil, vetiver oil, oliban oil, galbanum oil, labolanum oil and lavandin oil.
  • the dyes which can be used are those substances which are suitable and approved for cosmetic purposes, as compiled, for example, in the publication "Cosmetic Dyes” by the Dye Commission of the German Research Foundation, Verlag Chemie, Weinheim, 1984, pp. 81-106. Examples are culinary red A (CI 16255), patent blue V (CI42051), indigotine (CI73015), chlorophyllin (CI75810), quinoline yellow (CI47005), titanium dioxide (CI77891), indanthrene blue RS (CI 69800) and madder varnish (CI 58000). Luminol may also be present as the luminescent dye. These dyes are usually used in concentrations of 0.001 to 0.1% by weight, based on the mixture as a whole.
  • the total proportion of auxiliaries and additives can be 1 to 50, preferably 5 to 40% by weight, based on the composition.
  • the agents can be produced by customary cold or hot processes; the phase inversion temperature method is preferably used.
  • EQ1 palm fatty acid (Dehyquart® AU 56) EQ2 oleic acid and adipic acid (60: 4, Dehyquart® AU 04) EQ3 coconut fatty acid and adipic acid (60:40, Dehyquart® AU 93) EQ4 caprylic acid and adipic acid (70:30, Dehyquart® ABIO 8) EQ5 ricinoleic acid + 18EO
  • the fatty acid amidoamines used were exclusively condensation products of coconut fatty acid, which only differed in their amide components, namely:
  • Table 2 shows some recipe examples. Table 1
  • Hydagen® CMF 1.0 1.0 1.0 1.0 1.0 1.0 1.0 1.0

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  • Life Sciences & Earth Sciences (AREA)
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  • General Health & Medical Sciences (AREA)
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  • Veterinary Medicine (AREA)
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  • Epidemiology (AREA)
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Abstract

L'invention concerne l'utilisation pour produire des préparations cosmétiques, de mélanges contenant (a) des esters quaternaires et (b) des amidoamines d'acide gras.
PCT/EP2002/004374 2001-04-30 2002-04-20 Utilisation de preparations cationiques WO2002087536A1 (fr)

Priority Applications (2)

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JP2002584882A JP2004527550A (ja) 2001-04-30 2002-04-20 カチオン性製剤の使用
US10/476,553 US20040146478A1 (en) 2001-04-30 2002-04-20 Use of cationic preparations

Applications Claiming Priority (2)

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EP01110624A EP1254653B1 (fr) 2001-04-30 2001-04-30 Utilisation de compositions cationiques
EP01110624.2 2001-04-30

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EP (1) EP1254653B1 (fr)
JP (1) JP2004527550A (fr)
AR (1) AR034314A1 (fr)
AT (1) ATE275390T1 (fr)
DE (1) DE50103536D1 (fr)
ES (1) ES2231337T3 (fr)
WO (1) WO2002087536A1 (fr)

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JP4627055B2 (ja) * 2005-09-20 2011-02-09 株式会社資生堂 毛髪化粧料
ATE500813T1 (de) * 2006-09-11 2011-03-15 Kpss Kao Gmbh Haarfärbemittel
EP1929993A3 (fr) * 2006-12-05 2008-12-24 KPSS-Kao Professional Salon Services GmbH Composition de conditionnement pour des fibres de kératine
EP1929992A1 (fr) * 2006-12-05 2008-06-11 KPSS-Kao Professional Salon Services GmbH Composition de conditionnement pour des fibres kératiniques
DE102007027030A1 (de) 2007-06-08 2008-12-11 Evonik Goldschmidt Gmbh Stabile, niedrigviskose kosmetische Zusammensetzungen enthaltend Esterquats und/oder Dialkylquats
DE102007039954A1 (de) * 2007-08-23 2009-02-26 Henkel Ag & Co. Kgaa Reduktive Entfärbung keratinhaltiger Fasern
DE102008030136A1 (de) 2008-06-27 2009-12-31 Beiersdorf Ag Haarkonditionierende Zubereitung mit einer besonderen Mischung kationischer Konditioniermittel
JP5510948B2 (ja) * 2008-09-25 2014-06-04 東邦化学工業株式会社 化粧料組成物
JP4627333B2 (ja) * 2009-05-28 2011-02-09 株式会社資生堂 毛髪化粧料
JP4657354B2 (ja) * 2009-05-28 2011-03-23 株式会社資生堂 毛髪化粧料
DE102010026747A1 (de) 2010-07-09 2012-01-12 Beiersdorf Ag Haarbehandlungsmittel mit einem hohen Anteil an gebundenem Wasser
GB201111543D0 (en) * 2011-07-06 2011-08-17 Croda Int Plc Personal care compositions
EP2818155A1 (fr) * 2013-06-26 2014-12-31 Kao Corporation, S.A. Après-Shampooing
WO2018102050A1 (fr) * 2016-12-01 2018-06-07 Croda, Inc. Ingrédients destinés à être utilisés dans des compositions de soins personnels

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EP0786250A1 (fr) * 1996-01-23 1997-07-30 Henkel Kommanditgesellschaft auf Aktien Composition d'avivage pour la chevelure
EP0875500A2 (fr) * 1997-04-30 1998-11-04 Henkel Kommanditgesellschaft auf Aktien Amido-amine-étoxylates d'acides gras quaternisés
DE19743687C1 (de) * 1997-10-06 1998-11-26 Henkel Kgaa Detergensgemische und deren Verwendung
EP0885607A2 (fr) * 1997-06-19 1998-12-23 Henkel Kommanditgesellschaft auf Aktien Composition neutre et émulsifiante pour l'avivage des cheveux ou des fibres
DE19754283A1 (de) * 1997-12-08 1999-06-10 Henkel Kgaa Verwendung von Detergensgemischen
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EP0786250A1 (fr) * 1996-01-23 1997-07-30 Henkel Kommanditgesellschaft auf Aktien Composition d'avivage pour la chevelure
EP0875500A2 (fr) * 1997-04-30 1998-11-04 Henkel Kommanditgesellschaft auf Aktien Amido-amine-étoxylates d'acides gras quaternisés
EP0885607A2 (fr) * 1997-06-19 1998-12-23 Henkel Kommanditgesellschaft auf Aktien Composition neutre et émulsifiante pour l'avivage des cheveux ou des fibres
DE19743687C1 (de) * 1997-10-06 1998-11-26 Henkel Kgaa Detergensgemische und deren Verwendung
DE19754283A1 (de) * 1997-12-08 1999-06-10 Henkel Kgaa Verwendung von Detergensgemischen
DE19962874A1 (de) * 1999-12-24 2001-06-28 Cognis Deutschland Gmbh Transparente Avivagemittel

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JP2004527550A (ja) 2004-09-09
EP1254653A1 (fr) 2002-11-06
DE50103536D1 (de) 2004-10-14
ATE275390T1 (de) 2004-09-15
AR034314A1 (es) 2004-02-18
EP1254653B1 (fr) 2004-09-08
US20040146478A1 (en) 2004-07-29

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